


putting the work in

by troubleseeker



Category: Supernatural
Genre: Banter, Boss Castiel (Supernatural), Boss Jimmy Novak, Bottom Dean, Castiel and Jimmy Novak are Twins, DJC, Fluff, Incest, M/M, Multi, Office Sex, Oral Sex, Panties, Secretary Dean Winchester, Sexting, Spanking, Suits, Teasing, Threesome - M/M/M, Top Castiel, Top Jimmy Novak, because of twins
Language: English
Status: Completed
Published: 2019-02-21
Updated: 2019-02-21
Packaged: 2019-11-02 00:42:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,787
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17877866
Author URL: https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker
Summary: Dean Winchester is secretary to the twin presidents of Sandover inc, Jimmy and Castiel Novak. They call him into their office to dictate a letter, but things devolve quickly.





	putting the work in

“Dean, can you come in? We’ve got a couple of letters to dictate.”

Dean looked from his paperwork to the old fashioned intercom that sat next to his state of the art computer. It was a company heirloom or something, but it worked, so no one was getting rid of it. He set down his pen, and pressed the clunky yellowing button before leaning forward.

“Yes, sir. I’ll be right in.”

Taking a second, he organized his pile of papers. It would make it way easier to get started again when his bosses were done with him. Dean Winchester was nothing if not an efficient secretary. 

He had a color coded sticky note system that made it laughably easy to find everything.

His filing cabinets were immaculate.

He had the fancy coffee place and the doughnut shop down the street on speed dial. 

He was on good standing with at least one capable person in every part of the company, and knew every CEO’s secretary personally.

He could outtype anyone.

He even knew both his own, as well as his bosses’ calendars by heart.

“Oh. And bring the Wesson case.”

Dean slid the nearest filing cabinet open, and located the file in question in seconds. Again. Efficient.

“Yes, sir.”

Laptop and file in hand, he slid the placard next to the door to ‘in meeting’, and pushed his way into the massive office the presidents shared. He didn’t need prompting to lock the door. Dean had walked the walk before. He knew what he was doing.

Room secured, he strode over to the twin desks further inside the room. 

“Mr Novak. Mr Novak. The Wesson files, as requested”

Castiel smirked, reaching out to take the offered folder and plopping it down on the desk he was leaning against.

“Always so polite, aren’t you, Winchester?”

Dean wet his lips, and no, he wasn’t subtle about it. Jimmy copied the gesture from behind his mahogany monster; Dean tracked the movement out of the corner of his eye. 

“I do try, sir. You said something about dictating a letter?”

“Straight to the point.” Cas nodded, pushing away from his desk to deliberately step into Dean’s personal space. “Liked that about you from day one.”

“Anything else you like about me, sir?”

It was a blatant invitation - one they’d played with many times before.- and Cas was never one to turn down an invitation. He reached out to cup his secretary’s jaw, thumb flirting with Dean’s lips.

“Oh a good many things, Mr Winchester. You, Jimmy?”

The second twin finally rolled his chair back - Dean envied those chairs, they were just so God damn comfortable - and made his way around his desk. Eyes flitting all over Dean’s neatly suited body. Dean felt them linger on his ass, his chest, and his lips, before coming to rest on his eyes.

“Oh, a number of things, brother. A number of things.”

Dean grinned. Setting his laptop on the desk, making to open it up. 

“I’m flattered.”

His fingertips briefly brushed the edge of the computer, and then there were hands in his shirt; dragging him into Cas’s body and a heated kiss. 

“Been waiting to do that for  _ five _ hours.” He hissed, releasing Dean’s shirt to paw at his sides and ass instead. Dean moaned into the kiss, returning the affection in kind.

“Could have called me in sooner, and you know it.”

“And mess up your schedule? We wouldn’t  _ dare _ .” Jimmy pressed up behind Dean, joining Cas’s hands in messing up Dean’s suit.

“How very considerate of you, sir.” Dean panted. He was a lot younger than the twin owners of Sandover inc, but he was only the one man and they were very good at working as a team.

“And how very considerate of  _ you _ to send as such a lovely picture right as we sat down for our ten a.m. conference call.”

“I- ah- I know Jimmy has trouble staying awake when Zacharia starts talking numbers, sir.”

“As if I was paying even a lick of attention knowing what you were hiding under here.” Jimmy’s hands palmed Dean’s ass, rubbing up and down before squeezing harder.

“We’ve been mightily distracted all day.”

Dean gasped theatrically, arching his back to give Cas the space to undo his pants and also press his ass more firmly into Jimmy’s grip. 

“I am  _ so _ sorry, sirs. I swear my intentions were good.”

“I’m sure they fucking were.” Jimmy countered, pushing Dean’s slacks down once Cas had them unbuckled and unzipped - teamwork really was their forte. “Now show us your pretty panties before I get so distracted I bring the company down.”

Dean laughed, stepping out from between the twins to demurely lift his rumpled shirt to reveal midnight blue lace panties cradling his dick. 

“I’m buying you a new phone.” Cas rumbled, piercing blue eyes burning a hole into the delicate fabric. “That picture does not do this justice.”

“Turn around.” Jimmy ordered; voice wavering enough to lose the authority that made most of their competition tremble in fear.

Pursing his lips, Dean obeyed.

“I’m afraid you won’t be able to fuck me though, sir.”

Castiel’s hands - always less demanding than Jimmy’s - traced the outline of the lace trim framing his cheeks. 

“And why is that?”

“Because, oh fuck.” Dean paused, eyes rolling back as Cas’s fingers found the outline of his plug and  _ pressed _ . “Because you’ve got a face to face meeting with Crowley in an hour and I know neither of you have a spare suit here right now.”

Jimmy cursed, and Castiel sighed.

“We used our backup suits this weekend when Jimmy spilled tomato sauce everywhere.”

Dean nodded, canting his ass into the steady pressure against his prostate.

“But I’m so  _ distracted _ .” Jimmy whined from behind his brother. “Are you really going to let me go to a meeting like this?”

Cas stepped closer, expensive cotton pressing against Dean’s ass; erection obvious.

“I too, feel like I will be unable to concentrate on my work, Dean. Not like this.”

Dean laughed, grinding back against Cas dick for the fun of it. 

“That does sound like a problem a good secretary would solve.”

“Definitely.” Jimmy crowed, hand sneaking in between them to slide a sneaky fingertip underneath Dean’s panties as Cas hummed his agreement.

“Gonna have to let me up though, sir.”

Cas growled, and Dean felt his knees go weak. No way did he  _ even for a second _ regret seducing the Novak brothers like some 60’s romance novel secretary. 

“You’d better be planning on going down after I do, Mr. Winchester.”

Cas backed off, and Dean looked over his shoulder at them as he wriggled his ass; just for show. Jimmy smacked him for it, but he’d wear that print with pride. 

“When have I ever let you down, sir?”

Slacks around his ankles, Dean sank to his knees. 

“You haven’t yet.” Jimmy offered, hands working feverishly to unfasten his clothes. 

“And we appreciate your effort, of course.” Cass added, dick already free and straining as he offered it to Dean.

Dean smiled up at them from under his lashes, arms around both their legs to guide them closer together. 

“It’s only fitting, seeing all the  _ hard _ work you both do.”

Someone huffed a laugh above him, but Dean was too busy sliding Castiel’s dick into his mouth to concentrate on that. Both twins now plenty close, he reached up to take hold of Jimmy’s dick; stroking him gently as he worked his mouth down Cas’s shaft. 

There were fingers in his hair - probably Jimmy’s - pulling him off of Cas and towards the other needy appendage. Dean made a mental note to check his hair before he left the office. 

He switched between the both of them. 

Licking.

Sucking.

Gently edging them closer and closer to their individual peaks.

Their meeting wasn’t for another to hours, they had the time. Time to focus on Cas’s head, tongue digging into his slit just the way he loved it. Time to wriggle his tongue around across the bottom of Jimmy’s cock.

Time to hollow his cheeks and up the pressure bit by bit.

Time to gently relax his gag reflex and let them deeper, deeper, deeper. 

Time to bat his eyes up at the both of them as he blinked away wanna be tears. 

He had to shift his weight every so often to keep his knees in working order, and his legs awake. But it was so worth it. 

Worth it for the hands in his hair. The fingers on his ears, his neck, his jaw. Guiding him just as often as they begged for attention. 

Worth it for the moans. The gentle whimpers of pleasure that neither of them could allow to grow into moans or shouts. Locked doors kept out wandering eyes, but keen ears could walk down the hall, and that edge of danger heightened Dean’s own pleasure.

One hand pressed down on his own dick every so often. Adjusting and readjusting when he needed just  hint of relief. He wasn’t trying to come yet. His bosses came first, in every sense.

As they neared the edge, both twins dragged him in further. Cocks sliding deeper and faster. Hands rougher and more demanding as they pulled him off of their brother and onto their own erection.

Dean’s eyes rolled back, handing over full control to the twins and their needs. 

Castiel and Jimmy liked sharing him, but they both had alpha personalities and dear God he loved it when they started fighting over him. The rush of being desired,  _ needed _ even by such powerful - and attractive - men was insane. 

He’d lost track of who’s dick was who’s, sucking down what he was offered and whimpering in distress when he was pulled away, and breathing a sigh of relief when he saw his new target. 

He didn’t know who came first, hand still tugging diligently at the runner up as he swallowed what he was given. Moan muffled and barely safe.

“Are you nearly done, James?” Cas cut in from above, and Dean knew who’s dick was still weakly throbbing. The last of Jimmy’s load pulsing across his tongue when Cas pulled him back.

Three strong shoves later, Cas found his release deep down Dean’s throat. Dean pressed close, staring up at Castiel’s face, contorted in pleasure. When the soft suckle became too much, he pulled back; pressing a final kiss on Cas’s dick as a  _ see you later _ .

“Working your way straight to that raise there, Mr Winchester.” Jimmy giggled from the other side.

Dean pulled out his handkerchief, dabbing delicately at his eyes and mouth.

“I do aim to please, sir. Now, you did mention a letter?”

**Author's Note:**

> If you want to come yell at me on [tumblr](http://ryugarika.tumblr.com/) ... feel free to, I can take it.
> 
> Comments feed me!


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